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Pyrene-Terminated Tin Sulfide Clusters: Optical Properties and Deposition on a Metal Surface.

ABSTRACT: Herein, we present the synthesis of two pyrene-functionalized clusters, [(R^pyr Sn)₄ S₆ ]?2?CH₂ Cl₂ (4) and [(R^pyr Sn)₄ Sn₂ S₁₀ ]?n?CH₂ Cl₂ (n=4, 5?a; n=2, 5?b; R^pyr =CMe₂ CH₂ C(Me)N-NC(H)C₁₆ H₉ ), both of which form in reactions of the organotin sulfide cluster [(R^N Sn)₄ S₆ ] (C; R^N =CMe₂ CH₂ C(Me)N-NH₂ ) with the well-known fluorescent dye 1-pyrenecarboxaldehyde (B). In contrast, reactions using an organotin sulfide cluster with another core structure, [(R^N Sn)₃ S₄ Cl] (A), leads to formation of small molecular fragments, [(R^pyr Cl₂ Sn)₂ S] (1), (pyren-1-ylmethylene)hydrazine (2), and 1,2-bis(pyren-1-ylmethylene)hydrazine (3). Besides synthesis and structures of the new compounds, we report the influence of the inorganic core on the optical properties of the dye, which was analyzed exemplarily for compound?5?a via absorption and fluorescence spectroscopy. This cluster was also used for exploring the potential of such non-volatile clusters for deposition on a metal surface under vacuum conditions.

SUBMITTER: Geringer E

PROVIDER: S-EPMC7898349 | biostudies-literature | 2021 Feb

REPOSITORIES: biostudies-literature

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Pyrene-Terminated Tin Sulfide Clusters: Optical Properties and Deposition on a Metal Surface.

Geringer Eugenie E Gerhard Marina M Koch M M Krug Claudio K CK Gottfried J Michael JM Dehnen Stefanie S

Chemistry (Weinheim an der Bergstrasse, Germany) 20201217 8

Herein, we present the synthesis of two pyrene-functionalized clusters, [(Rpyr Sn)4 S6 ]⋅2 CH2 Cl2 (4) and [(Rpyr Sn)4 Sn2 S10 ]⋅n CH2 Cl2 (n=4, 5 a; n=2, 5 b; Rpyr =CMe2 CH2 C(Me)N-NC(H)C16 H9 ), both of which form in reactions of the organotin sulfide cluster [(RN Sn)4 S6 ] (C; RN</s ...[more]

PMID: 32936477

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Project description:π-Extended pyrene compounds possess remarkable luminescent and semiconducting properties and are being intensively investigated as electroluminescent materials for potential uses in organic light-emitting diodes, transistors, and solar cells. Here, the synthesis of two sets of pyrene-containing π-conjugated polyaromatic regioisomers, namely 2,3,10,11,14,15,20,21-octaalkyloxypentabenzo[a,c,m,o,rst]pentaphene (BBPn) and 2,3,6,7,13,14,17,18-octaalkyloxydibenzo[j,tuv]phenanthro [9,10-b]picene (DBPn), is reported. They were obtained using the Suzuki-Miyaura cross-coupling in tandem with Scholl oxidative cyclodehydrogenation reactions from the easily accessible precursors 1,8- and 1,6-dibromopyrene, respectively. Both sets of compounds, equipped with eight peripheral aliphatic chains, self-assemble into a single hexagonal columnar mesophase, with one short-chain BBPn homolog also exhibiting another columnar mesophase at a lower temperature, with a rectangular symmetry; BBPn isomers also possess wider mesophase ranges and higher mesophases' stability than their DBPn homologs. These polycyclic aromatic hydrocarbons all show a strong tendency of face-on orientation on the substrate and could be controlled to edge-on alignment through mechanical shearing of interest for their implementation in photoelectronic devices. In addition, both series BBPn and DBPn display green-yellow luminescence, with high fluorescence quantum yields, around 30%. In particular, BBPn exhibit a blue shift phenomenon in both absorption and emission with respect to their DBPn isomers. DFT results were in good agreement with the optical properties and with the stability ranges of the mesophases by confirming the higher divergence from the flatness of DBPn compared with BBPn. Based on these interesting properties, these isomers could be potentially applied not only in the field of fluorescent dyes but also in the field of organic photoelectric semiconductor materials as electron transport materials.

Dataset Information

Pyrene-Terminated Tin Sulfide Clusters: Optical Properties and Deposition on a Metal Surface.

Publications

Pyrene-Terminated Tin Sulfide Clusters: Optical Properties and Deposition on a Metal Surface.

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